Accurate estimates of item difficulty are essential for valid assessment and effective adaptive learning. However, for newly created tasks, response data are typically unavailable. Pretesting and expert judgement can be costly and slow, while machine learning methods often require large labelled training datasets. Recent work suggests that large language models (LLMs) may help. However, there is limited evidence on the elicitation procedures and prompt configurations used to emulate experts for difficulty estimation. This study addresses this gap by evaluating three off-the-shelf LLMs as difficulty raters for newly created items without access to response data. Using an item bank from an online learning system, the study examined 6 domains of primary-school mathematics, with empirical difficulty estimates treated as empirical reference. The study used a full factorial design crossing three factors: judgement format (absolute vs pairwise), decision type (hard decisions vs token-probability-based estimates), and prompting strategy (zero-shot vs few-shot). LLM-derived difficulty estimates were compared with empirical difficulties using Spearman rank correlations. Across domains, LLM-based estimates exhibited moderate to strong positive correlations with empirical item difficulties. For simpler arithmetic tasks, some configurations approached the upper end of the accuracy range reported for human experts in previous research. Pairwise comparison consistently outperformed absolute judgement in the absence of additional refinements. However, when token-level probabilities were incorporated and examples of items with known empirical difficulty were provided, the absolute judgement configuration likewise demonstrated moderate-to-high alignment. The study positions LLMs as a promising tool for initial item calibration and offers insights into effective workflow configuration.

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